Certain substituted propyl acrylate and methacrylate esters are known in the art. U.S. Pat. No. 4,192,685 describes compounds which have the formula ##STR3## wherein n is an integer of at least 1, p, q, and r is 0 or an integer of at least 1 with the proviso that p+q+r equals to 2-6, R.sup.1 is a hydrogen or a methyl group, R.sup.2 is a lower alkyl group optionally substituted with a halogen atom, and R.sup.3 is an alkyl, aryl or acyl group optionally having a substituent. These compounds are said to be useful in photocurable resin compositions.
It is known in the art to esterify hydroxyl groups bonded to alkyl groups of both hydroxyalkyl acrylates and methacrylates. U.S. Pat. No. 3,470,124 describes monomers of the formula R'COO--Y--OOCR", wherein R'COO is a perfluoroalkanoic acid residue; R"COO is a residue of a polymerizable alkenoic acid; and Y is a residue of an organic compound selected from the group consisting of aliphatic, aliphatic-aromatic and aromatic dihydric alcohols as well as the functional derivatives thereof. The functional derivatives refer to the precursors of the dihydric alcohols. No functional derivatives of Y are listed or shown in the examples. Only methyl derivatives are exemplified. No derivatives which include halogen or ester derivatives of the Y moiety of the monomers are mentioned. These monomers are prepared by usual esterification methods known in the art and are oleophobic viscous oils and are useful in treating fibers, paper, wool, brick, etc. to make them oil-resistant.
British Pat. No. 1,118,007 describes hydroxyalkyl (meth)acrylate esters of perfluoroalkanoic acids and their polymers. They claim monomers which provide polymers with at least three perfluorinated carbon atoms which possess hydrophobic and oleophobic properties and are useful for coating materials and sizing cloth to give resistance to soiling. U.S. Pat. No. 3,459,722 describes the reaction of hydroxyethyl methacrylate with 2-(perfluoro-n(or iso)-propoxy)perfluoropropionyl fluoride to provide the expected ester, 2-(perfluoro-n(or iso)-propoxy) perfluoropropionoxyethyl methacrylate, which is useful for treating fabrics and yarns to render them repellant to oil and water. U.S. Pat. No. 3,595,944 describes polymers containing 2H,2-perfluoropropyl acrylate, which provide oil- and water-repellant compositions.
Reactions of trifluoroacetic anhydride are described in Dear, Intrascience Chemistry Reports, Vol. 5, No. 1, 37 (1971). It is reported there (page 45) that: "Derivatives of acrylic and methacrylic acid have been polymerized by heating with a mixture of trifluoroacetic anhydride and an amine oxide". No reactions of trifluoroacetic anhydride with epoxides are reported.